Triethylamine → Tert-butyl {1-[2-(methylsulfanyl)ethyl]piperidin-4-yl}carbamate

HRID 1928749Notes

Reaction equation

[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[CH2:23][CH2:24][S:25][CH3:26]>CO>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:23][CH2:24][S:25][CH3:26])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

Piperidin-4-yl-carbamic acid tert-butyl ester (0.70 g, 3.0 mmol), triethylamine (1.46 mL, 10 mmol) and 2-chlorethyl-methylsulfide (0.39 g, 3.0 mmol) were dissolved in methanol (10 mL) and stirred for 16 h at 50° C. Then the solvent was removed and the residue subjected to column chromatography (silica gel, heptane:ethyl acetate gradient=1:1→0:1). [1-(2-Methylsulfanyl-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester was obtained as a light yellow solid (0.46 g, 48%); MS: m/e=275.5 (M+H+).

Workup

customThen the solvent was removed

Sources & evidence

ORD record: ord-98dcaae06bb14708a0c3991db097a8c7
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183380B2

Reaction notes

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